A New Side Of Life
by rainbowsandsunshine123
Summary: Take place after S7. Follow Rory and Jess on their journey as they are presented with one of life's most precious gifts. Literati JavaJunkie
1. Chapter 1

Rory leaned against the sink, heaving as another wave of nausea hit her. It was only a few seconds before she was right back at her place in front of the toilet bowl puking her guts out. She felt as though there were butterflies zooming around in her stomach, and not in the good kind of way. No it was the kind of way that made her want to smack her head against the tiled floor again and again. Needless to say it wasn't a good feeling.

"Ror that's like the fifth time this week. That's not normal." She looked up to see Jess walk into the bathroom attempting to adjust the tie around his neck. All these years later and he still found fastening a tie around his neck an almost foreign concept.

"Come here." She grumbled from her place om the ground as she wiped her face on a towel. Rory had taken it upon herself to teach herself how to tie one.

Jess walked towards her and she hoisted herself up. Jess reached out to help her. "Rory I'm serious. Go see the doctor. Please."

"Jess. I'm fine." She pushed the knot up towards his neck. "It's probably food poisoning from that Thai food that we had on Thursday. Nothing us Gilmore women can't handle."

He rolled his eyes. "First of all you're a Mariano now." This earned him a shove and a smirk form his wife. "And second that was like five days ago. I highly doubt that food poisoning would have lasted this long." He answered. "Look if its that than okay at least we'll feel better after getting it checked out. Please go. For me." And then he gave her his best puppy dog eyes. Something he would not have been caught dead doing a mere eight years ago. But the again a lot had changed over the past seven years.

"You know how I feel about the doctors. Lots of unnecessary looks and needles." But when she saw how adamant Jess looked about the situation she decided that it wasn't worth the fight and she gave in. To be honest she wasn't totally convinced that it was food poisoning either. "But I'll go." She looked over at him. "Bur just for you. And only if you promise we can binge watch Gossip Girl with four different types of ice cream."

"Two."

"Three and we have a deal if you throw in gummy bears."

…

"So do when do we tell everyone."

Jess and Rory were sprawled out on the couch in the living room. The TV was on playing some sort of cupcake show that they weren't watching.

"Well I guess as soon as possible."

"So tomorrow?"

"I feel like we should tell my mom and Luke and your mom in person. I don't think they'd appreciate hearing it over the phone,"

"Well they should just appreciate it period."

"Jess." Rory said looming over at him. "Don't you want to see the looks on their faces when we tell him. I mean we just won't get that same effect over the phone."

"Yeah I'm just dying to get a glimpse at their looks of shock." Jess responded.

"Jess come on. You know that isn't true. They're all going to be super happy for us."

"If they don't all die form shock first."

Rory rolled her eyes as she threw a couch pillow at him. "It's going to be fine. Everyone's going to be psyched. And we're going to be"

"Parents." He finished for her. "We're going to be parents."

Rory turned her head to look him in the eye, her hand subconsciously finding its way to her stomach. "Jess how do you really feel about this?" They'd been married for about a year and a half and of course the subject of children had come up. But it hadn't exactly been something they had discussed in depth. She guessed they both assumed that it would happen when it happened. They hadn't done anything to prevent it, knowing it was something they wanted in the future. But they didn't think that future would come so soon.

Jess was quiet for a few seconds which terrified Rory slightly, before he finally spoke. "I'm happy." He answered as his hand covered hers. "Its something I want." He kissed her head. "It's definitely something I want with you."

Rory's heart melted. She loved this new mature side of Jess. He definitely wasn't the same seventeen year old boy she had once knew. She liked to think that this side of Jess was hiding in that version of him all along. It just needed time to thaw.

"Me too." She said snuggling into him. "So I guess that's it. We're having a baby.'

"We're having a baby." He confirmed as he leaned in to kiss her.

…

 _August 25, 2006_

 _Rory stood in front of the door, her nerves running wild. She had been envisioning this moment for months and she couldn't believe that she was actually living out the events that had taken place in her mind for some long. She took a deep breath as she opened the door and walked inside. It looked almost the same as it had almost a year ago when she had come to the grand opening. But now she was in a very different position the she had been in the last time she had walked through the door._

 _"_ _Can I help you?" A voice thrust her out of her thoughts. She realized that she had been staring at the wall of books longer than what would be considered normal. Looking up she found herself come face to face with a guy she vaguely found familiar._

 _"_ _Oh…um…hi." Rory stuttered out._

 _The guy looked at her strangely as he answered. "Hi."_

 _"_ _Um I was looking for Jess?" She finally got out, sure that she was about to pass out, She didn't know why this whole situation was making her so nervous._

 _"_ _You're looking for Jess?" The guy repeated as he analyzed the woman in front of him._

 _"_ _Yes."_

 _"_ _And you are-"His words were cut short as footsteps approached them._

 _"_ _Hey do you know when we're getting the shipment pf the Stevens book?" Rory's heart stopped as she heard a voice that as all too familiar to her call out to the man who stood before her._

 _"_ _I thought they were supposed to get here last" He stopped mid sentence as she saw who was talking to his friend._

 _"_ _Rory?" He asked in confusion, running a hand through his hair. 'What are you doing here." "Hey Jess."_

 _A couple hours later they found themselves on Jess' couch. After their somewhat awkward reunion they had made their way to a coffee shop down the street to talk. Rory told him all about her news job. She loved working on the campaign trail and she found herself opening up to him easily. Almost as if things hadn't been weird between them. In return he told her about how Truncheon was going: very successfully. It was a hit and there were talks of opening up a new location in New York. And though it seemed like they talked about everything and anything, in reality they hadn't even scratched the surface. Feeling the tension that was starting to settle in between Jess invited Rory to come see his apartment._

 _"_ _What are you doing here Rory." Jess asked, finally asking the question that had been bugging him for the past couple of hours._

 _"_ _I told you. I had a few days off."_

 _"_ _I get that. What I'm trying to ask is why? Why did you come here to see me?"_

 _Rory sighed as she she leaned forward. Obviously she knew that this whole situation was strange. Why had she spent her day off driving all the way here? Why did she find herself in front of Truncheon? Why had she come looking fro him? Subconsciously she knew the answers to these questions but getting them out in the open was proving to be the difficult part. "I don't know." She finally let out. "I guess I wanted to see you. We didn't exactly end on the best of terms last time we saw each other." She waited for him o answer when she realized he was waiting for her to continue. "And I know that was my fault. But I just wanted to set things straight I suppose."_

 _"_ _You came all the way over here to set things straight?" He asked with a raised eyebrow. "After no communication for so long you didn't think a phone call would suffice?"_

 _He was doubtful. She got that. He had every right to be. It was the way things had been between them for the past few years. "I miss you." She buried her head in her hands, almost embarrassed for saying that out loud. "I just…I just feel like like technically I have my life together. But I feel different. And I know that I'm grown up now and things have changed. But I feel like there's nothing familiar anymore. And I just needed to come here and see you. Get a feel of how my life was before." She tried to explain_

 _"_ _Rory I think it's safe to say that we're both different people now."_

 _"_ _He asked me to marry him." She blurted out. A look of shock registered on Jess' face. But before he had a chance to respond she continued. "I said I wasn't ready and he left." She bit her lip, trying to hold back the tears that were threatening to cascade down her face. "You were right when you said I was doferent. And I don't think I wanted to admit it then."_

 _Jess looked at her. "Rory I didn't mean to"_

 _"_ _I know. But like you said you know me better than anyone right." She laughed through her tears. "I guess I'm trying to tie up lose ends. And me and you definitely need some tying up."_

 _"_ _We've just never had the best timing."_

 _"_ _Maybe we just haven't until now."_

 _…_

"Omg Rory!" Lane exclaimed as she rushed over to give her best friend a hug. "I'm so happy for you and Jess."

"Thanks Lane." Rory replied, hugging her back. 'We figured it was time to give Steve and Kwan a cousin."

"Ah they're going to be so excited." She said. "Did you tell Lorelai yet?" She asked.

"We her and Luke last night."

"And" Rory prompted. "How'd they react?"

"Well my mom was through the roof. You know a comment here and there about being a grandma so young." Rory laughed. "And Luke well it took him a moment to digest the news."

Rory's mind traveled back t the previous night. Her and Jess decided to head into Stars Hollow for the weekend to tell everyone. They had gotten in right around dinner time. And though Rory and Jess had decided that they would wait until after dinner to break the news. Rory couldn't stand sitting across from her mother not knowing what she knew so she just blurted out the news. Lorelai had jumped out of her seat the minute the words left her mouth and attacked Rory with a hug. As for Luke, he sat there for a minute or two and asked if they were sure. And when Jess confirmed the news he stood to give both of them a hug. Rory knew the news had definitely shocked Luke. Even though Jess was not the same guy he was who had waltzed into Stars Hollow all those years ago it was still hard for Luke to process. But he was excited and started rattling off things Rory should stay away from with her mother refuting everyone.

"Luke asking a Gilmore to gave up a coffee is like asking fish to give up water." Which sent them into a bickering session.

But Rory couldn't be happier. Right at that moment she had it all. A husband who adored her. A mother who was her best friend. A step dad who wanted nothing but the best for her. And a baby on the way.

 **Hey guys! So in light of the Gilmore Girls reunion I thought I would right this! I thought I would get my what I imagined the show to go like out before that lol.**

 **But I hoped you guys enjoyed it! Reviews would be greatly appreciated! Let me know what you think! Should I continue?**

 **I thought I would include flashbacks of their lives leading up to that moment. What do you guys think?**


	2. Chapter 2

**Let me know what you guys want to see!**

"How're you feeling honey?" Lorelai asked as she juggled the phone between her head and shoulder.

Rory was shifting through the mail as she balanced the phone. "Okay. I still have morning sickness. But I guess that's to be expected." She stopped shuffling when she got to an envelope addressed to her. Seeing the senders name and address, she ripped open the envelope desperate to read its contents. "Oh my god Mom. You will not believe what I'm holding in my hand at this very moment."

"Let me guess. It's a check for a bajillion dollars and you're gifting it to you're most favorite maternal figure in your life."

Rory laughed, rolling her eyes. "Crazier. It's a wedding invitation' She paused wanting wanting to build up the suspense, "To Paris and Doyle's wedding."

"What?" She heard her mother exclaim from the other line. "When did they even get engaged?"

"I don't even know." Rory read over the piece of paper in her hands. "But apparently they're having it in…Stars Hollow?" She said confused. "Stars hollow? Why would it be in Stars Hollow? She's not even from there!" Rory couldn't help but laugh at the thought of Paris and Doyle getting married in a place she once considered a creepy small town. "I guess I'll have to call her later and get the details."

"Well you're definitely going have to call me as soon as that conversation is over." Lorelai reciprocated the laugh. "So when are you going to tell my mother, you're grandmother about the precious cargo you're carrying around."

Rory groaned. She had almost forgotten. Of course she knew that she had to tell her grandparents. She just didn't know exactly how they would react. Her grandmother had never exactly approved of Jess. The seventeen year old boy who had arrived to dinner with a black high and bad attitude was still etched into Emily Gilmore's mind. Sure she had thawed a bit. She had taken part in the wedding prep and Richard had even made an attempt to get to know Jess. But Rory knew that in their minds no one would ever be good enough for her.

"I know." She sighed. "I just can't find the perfect moment."

"Sorry to break it to you hon, but it'll never be the perfect time. Wow déjà vu huh. I remember when I was scared to tell my parents that I was pregnant."

"Not funny Mom. I really am nervous."

"Rory you and Jess are married. You both have jobs and lives. You have nothing to be nervous about. You're having a baby and you're ready. And I'm sure my parents are going to be thrilled."

…

Rory and Jess stood hand in hand in front of the huge house she knew so well.

"We doing this?" Jess asked, shoving his hands into his pockets. He was obviously nervous.

"We're doing this." Rory confirmed as she rang the doorbell. A few seconds later a mousy looking woman answered the door. Emily had changed maids once again. She led them inside as she took their coats.

"Your grandmother and grandfather are waiting for you in the living."

"Here we go." Rory breathed out as Jess grabbed her hand.

Twenty minutes late they found themselves at the dining room. Conversation was flowing freely. Richard and Jess were engrossed in a conversation over Truncheon. Jess was thinking about opening a new store, in addition to one they had opened in New York and Richard was jumping in with suggestions.

And Emily had been asking her about how life was going in New York and for a second Rory wondered why she had been so nervous over this whole thing. They weren't teenagers anymore. And to be honest, being afraid of what her grandparents would think of a baby coming into this was was absolutely insane. Of course they would be happy. There was no reason they wouldn't be.

"So Grandma, Grandpa we actually have something to tell you." Rory glanced over at Jess who looked calm, cool, and collected. She felt him squeeze her hand from under the table, offering his support.

"Well." He grandmother prompted. "What's going on? Is everything alright" She had stopped eating, setting her spoon down as she dabbed at her mouth with a napkin.

"Well recently Jess and I found something very interesting." She paused. "I'm pregnant." She announced. No one said anything for a couple of seconds. Rory looked at her grandparents in apprehension, not knowing exactly what their reactions were.

Emily's face broke out into a huge smile as she exclaimed. "Really? Are you sure."

And Richard responded with, "Well I'll be. Isn't that just fantastic news."

And at that moment Rory let out the huge sigh she hadn't even been aware that she was holding. "I'm sure." Rory answered laughing slightly as tears gathered in her eyes. Now that they knew it was real. It finally hit her that this was all happening. The last few weeks had been filled with thoughts about the baby, but not until that very moment did the thought of another little member joining their family hit her. Her grandparents had been such an important of her life for so long and to have them involved in such a big change meant so much to her.

"Oh my. This is so exciting." Her grandmother leaned forward in her seat, already in planning mode. "Oh this is going to be so fun. I saw the cutest little jumpers in the store the other day. And oh you'll have to find out what you're having so we can pick a theme for the baby shower." Emily rattled on and on about parties and clothes. But Rory was to happy to give any thought to that at the moment.

She and Jess both looked at each other and just smiled.

…

 _February 17, 2007_

 _"_ _When are you going home again?"_

 _Rory laughed on the other line as she shuffled her papers back into place. "I've told you like a million times Jess. A couple of days."_

 _"_ _I just wanted to make sure that I had the facts straight." Jess said on the other line. He was currently packing clothes into an open suitcase on his bed._

 _"_ _You're heading there tonight right?"_

 _"_ _Yeah. I can't believe I'm actually heading back to Stars Hollow."_

 _"_ _It's going to be great.' She exclaimed. "Plus I totally don't buy your whole 'I hate Stars Hollow' act."_

 _"_ _Hey! I'm only going back there for you!"_

 _Since their last meeting, Rory and Jess had found a way to be a part of each other's lives. Phone calls were a daily ritual between the two. And they literally spent hours upon hours discussing everything frmo the latest books that they were reading to the weirdo who lived in the apartment next to Jess. The phone calls were soon coupled with quick visits: Rory going up to see Jess in Philadelphia any weekend she had off and Jess driving out to wherever the campaign was the few days that he could scrounge up. Soon their friendly conversations tuned into flirty conversations and hugs that lasted a but too long. In all honestly it didn't take all that long. Their history was hard to ignore and being friends was really just a way to enter into something they both wanted._

 _And though they agreed to take things slow, for Rory and Jess that simply wasn't possible. They had waited a long time to get to the place they finally were at. First they had been two teenagers, not really ready for the kind for the kind of relationship they had and the kind that it could become. And after that the timing just wasn't right. At that point in her life Rory truly believed that she needed to be with Logan. After all all of that had led the to this very point in time. They weren't kids anymore and they were both ready for a real and mature relationship. And this time they were both hell bent on making it work. Neither of them could deny the aching inside of their hearts that was telling them that this was it. That they had both finally found the person that they were really supposed to be with._

 _"_ _So I was going to wait to tell you this when I saw you but I anticipate that things are going to be pretty crazy when we get to Stars Hollow." Rory was returning home after a while and Jess knew that all of the town would be vying for time with her._

 _He took a deep breath before he continued. "We're opening the next Truncheon in New York."_

 _"_ _Really?" Rory asked, doing everything she could to not burst out screaming at that very moment._

 _"_ _Yeah, we got approved for the building."_

 _"_ _Jess this is great. I can't believe it." She breathed out._

 _"_ _I told you everything would work out." And Rory knew that at that moment he was supporting a smirk she knew all too well._

 _Nto only was Rory going home after a while. Her time with the Obama campaign had come to an end. And waiting for her at the end of that rainbow was a job at the New York Times Yes, that as right she, Rory Gilmore, was going to be working at one of the most prestigious newspapers in the country and she was thrilled. But the downside to the whole situation had been the fact that Jess was running Truncheon in Philadelphia. To think that they had waited all those years to finally make it work between themselves and distance was going to get in the way really sucked. But the fact that Jess would potentially be moving to New York with her just made this all seem like a dream come true._

 _Rory had known that Jess and the guys had been looking to open a new store. And they had been throwing around different locations for a while. New York had been one of the ones at the top of the list. But they had been iffy on whether or not they were going to get the place they had found._

 _Everything was falling into place. Almost like it was all meant to be._

…

Rory walked through the front door of their apartment and dropped her bag and keys on the table. And then she promptly dropped herself on the couch next to it. She was exhausted. It had been a particularly tiring day at work and she wanted nothing more than to put her feet up and relax. But just as she was about to prop her feet up on the coffee table in front of her and turn to the TV on she realized that she would never get to enjoy all of the eating and TV watching she had been planning all day in the outfit she was currently supporting. She needed to get her junk food sweat pants on fast.

So she walked into the room and pulled out a t-shirt and yoga pants form her drawer. But when she pulled off her blouse she gasped.

"Jess get in here!"

And only a mere few minutes later he rushed into the room. He had been all day working on his newest book when he had heard Rory call out. "What's the matter?" He asked frantically. Is everything all right?"

She tuned to face him in her bra. "Do you see it?"

"See what?" He asked in confusion.

"It" She said pointing to her stomach. "I'm showing!"

And true to her word, there was the slightest indication of their baby growing inside of her.

"That's amazing." Jess whispered, as he crouched down and lightly ran his hand over her bump. "I mean that's our baby in there."

"I know." Rory placed her hand over his. "It's crazy. This is really happening."

Rory was now three months pregnant and she still had all of the pregnancy symptoms. Jess still woke up to her throwing up almost every day of the week. And needless to say she had been getting more tired than usual. But the appearance of that little bump was absolutely incredible. It was a blatant reminder of what was about to come.

Jess got up form his place on the floor and Rory slipped the t-shirt on over her head. "What do you say in light of this moment we order pizza and watch Friends?"

Jess laughed as he leaned in to kiss her. "Sounds good to me.

…

"Rory! My savior! Save me from this evil man he's trying to get me to eat veggies!" Lorelai yelled, ambushing her the minute she walked through the door.

Luke followed closely behind her. "She's being ridiculous. All I suggested was having carrots with our chicken." He rolled his eyes.

Rory had to laugh at that. Her mom and Luke were still the same. She was so glad that they had worked things out all those years ago. They really were meant for each other. They had gotten married a couple of years back and Luke had taken up residence in the Gilmore house permanently. Although now she supposed it was the Danes house.

"Hey guys." She heard Jess greet as he set down their bags. Unlike most of their trips to Stars Hollow they were going to be staying the weekend this time. It wasn't something they did often. New York was only a few hours away from Stars Hollow and they usually didn't extend their visits past the day. But lately Rory had been feeling homesick and she needed a few days in her town.

"So Aprils going to be coming in a couple of hours and she's so excited to see you both." April was now in High School and Rory saw so much of herself in that girl. She usually spent the weekends with her dad and Luke and Lorelai had renovated their house once again, adding in another bedroom for April.

"I put fresh sheets in your room and there are towels in the bathroom. And well you know where everything is really." Lorelai rattled on as they followed her into the kitchen, "So I'll let you guys settle in and then we'll take a walk around town?"

Rory nodded in response. "Sounds great Mom."

"Okay well I'll leave you two to it." She closed the door behind her as Rory took in her old room. Everything was jus the way she had left it. All of her Yale paraphernalia still adorned the walls and the shelves were still covered with the all the books that Rory had indulged in during her High School years. It seemed as though time had stood still in that little corner of the world.

Jess plopped down on her bed. "Man this bed seems tiny."

"Yeah it might be time for a bed upgrade." Rory agreed as she took a seat next to him.

"I mean maybe we'll have a different bed, much bigger bed in Stars Hollow."

Rory did a double take, confused. "What are you talking about?"

"How would you feel about moving back to Stars Hollow?"

 **So I realize it jumps around a lot. Sorry! I just have so many things that I want to address.**


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